WO2008046796A2 - Utilisation de c10-c14-alcane-1,2-diols pour l'élaboration d'une composition destinée à la prophylaxie et/ou le traitement d'infections à dermatophytes - Google Patents

Utilisation de c10-c14-alcane-1,2-diols pour l'élaboration d'une composition destinée à la prophylaxie et/ou le traitement d'infections à dermatophytes Download PDF

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WO2008046796A2
WO2008046796A2 PCT/EP2007/060918 EP2007060918W WO2008046796A2 WO 2008046796 A2 WO2008046796 A2 WO 2008046796A2 EP 2007060918 W EP2007060918 W EP 2007060918W WO 2008046796 A2 WO2008046796 A2 WO 2008046796A2
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oil
polyethylene glycol
alkane
diols
acid
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WO2008046796A3 (fr
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Gerhard Schmaus
Sabine Lange
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Symrise AG
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Symrise AG
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations

Definitions

  • C10-C14-alkane-1 ,2-diols in the preparation of a composition for the prophylaxis and/or treatment of dermatophyte infections
  • the present invention relates to the use of one, two, three or more C10-C14- alkane-1 ,2-diols in the preparation of a composition for the prophylaxis and/or treatment of dermatophyte infections, and to cosmetic and/or dermatological preparations for topical application comprising or consisting of one, two, three or more C10-C14-alkane-1 ,2-diols.
  • Dermatophytes are a special group of fungi which have become adapted to and specialised in growing on the skin, in the hair and in the nails. Because they are specially provided with enzymes such as keratinases, elastases and collagenases, they are able to break down the proteins and structures in human skin, establish themselves and accordingly cause infections. The infections generally remain locally limited, and for this reason the typical syndromes are named according to the affected areas of the body. An infection by dermatophytes is referred to medically as "Tinea”.
  • Tinea pedis foot
  • Tinea manuum hand
  • Tinea capitis head
  • Tinea corporis upper body
  • Tinea barbae beard
  • Tinea faciei face
  • the most well-known form is definitely athlete's foot.
  • a broad European study Achilles project
  • about one in four Germans suffer from athlete's foot at least occasionally.
  • One in seven has an infection of the nails (Tinea unguium or onychomycosis). Because these infections do not manifest themselves as an unpleasant phenomenon until a very late stage, owing to the slow growth of the fungus, they are often not noticed in the initial stages.
  • Treatment is only introduced when, after initial itching and burning, there is also a clearly visible change in the affected parts of the body or skin. However, the later treatment is started and the further the infection has progressed, the more difficult is successful therapy.
  • Trichophyton species such as Trichophyton mentagrophytes and Trichophyton rubrum. More than half of all cases of athlete's foot can be attributed to these species.
  • Further important dermatophytes are Epidermophyton floccosum, Microsporum gypseum and Microsporum canis. These dermatophytes are often to be found in the human environment in communal changing rooms and in swimming baths and sports halls. Some are also strongly associated with pets (Microsporum canis) and are to be found in stables, straw and feeds. Objects such as cushions, covers and toys, which are in close contact with pets, can also be regarded as sources of dermatophytes and possible infections.
  • Microsporum gypseum occur especially in the ground and lead to infections and occupational diseases of the hands (Tinea manuum) in gardeners and agricultural workers.
  • Tinea unguium onychomycosis
  • the nail infection, Trichophyton and Epidermophyton species in particular play a fundamental role.
  • Inhibiting the growth of dermatophytes of the genera Trichophyton, Epidermophyton and Microsporum represents the main method of controlling dermatophyte infections.
  • Effective therapies against dermatophytes are possible using various active ingredients.
  • the most common active ingredients at present are indicated hereinbelow, a distinction being made between active ingredients for topical treatment and for systemic treatment.
  • Topical treatment local therapy with representatives of recognised active ingredient classes such as
  • azoles e.g. clotrimazole, miconazole, econazole, bifonazole, sertaconazole;
  • hydroxypyridones e.g. ciclopiroxolamine
  • allylamines e.g. terbinafine or naftifine
  • ketoconazole especially ketoconazole, itraconazole or fluconazole;
  • the active ingredients are applied locally either in the form of ointments, sprays or tinctures or, in the case of Tinea unguium (onychomycosis), also in the form of special nail lacquers.
  • systemic treatment by oral ingestion is necessary if relatively large areas of the body are already affected or the infection has penetrated into deeper layers of the skin.
  • administration is in the form of, inter alia, tablets, capsules, dragees, powders, juices or suppositories.
  • sensitisation reactions are increasingly being observed in clinical practice for azole derivatives when applied topically.
  • Tinea is associated with high stress on liver functions because of the necessary ingestion of relatively large amounts of active ingredients over a prolonged period.
  • the object of the present invention was, therefore, to provide a compound and a cosmetic and/or dermatological preparation for topical application which inhibit the growth of dermatophytes, preferably of dermatophytes selected from the group consisting of Trichophyton, Epidermophyton and Microsporum species, more preferably Trichophyton mentagrophytes and/or Epidermophyton floccosum, and at the same time are well tolerated by the skin at the particular effective concentration and are preferably non-irritant, non-itching, non- sensitising and/or non-carcinogenic.
  • dermatophytes preferably of dermatophytes selected from the group consisting of Trichophyton, Epidermophyton and Microsporum species, more preferably Trichophyton mentagrophytes and/or Epidermophyton floccosum
  • An embodiment of the present invention relates to the use of one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably of a compound or of a mixture of two or three compounds selected from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, in the preparation of a composition for the prophylaxis and/or treatment of dermatophyte infections.
  • a further embodiment of the present invention relates to the use of one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably of a compound or of a mixture of two or three compounds selected from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, as a cosmetic composition for inhibiting the growth of dermatophytes.
  • a further embodiment relates to a cosmetic and/or dermatological preparation for topical application, comprising or consisting of:
  • auxiliary substances and/or additives optionally one, two, three or more auxiliary substances and/or additives.
  • C10-C14-alkane-1 ,2-diols within the scope of the present invention contain an unbranched alkane chain, the OH functions being located in the 1- and 2-positions of the alkane chain, and include both (a) enantiomers having the 2S configuration and (b) enantiomers having the 2R configuration as well as (c) any desired mixtures of C10-C14-alkane-1 ,2-diols having the 2S and 2R configuration.
  • the improvement in the condition of skin damaged by dermatophyte infections is based on the property of the C10-C14-alkane-1 ,2-diols according to the invention of inhibiting the dermatophytes of the genera Trichophyton, Epidermophyton and Microsporum, preferably Trichophyton mentagrophytes and/or Epidermophyton floccosum, which are substantially involved in dermatophyte infections.
  • JP 51 91327 to the bacteriostatic action of alkane-1 ,2-diols against particular microorganisms in connection with the preservation of foodstuffs and cosmetics, but no antimicrobial action of the alkane-1 ,2-diols against dermatophytes, such as especially representatives of the genera Trichophyton, Epidermophyton and Microsporum, the microorganisms that play a part in dermatophyte infections, is disclosed.
  • JP 2002 2003330 describes the antibacterial action of a combination of 1 ,2-alkanediols and ascorbic acid esters, but this specification contains no reference to an antimicrobial action of the alkane-1 ,2-diols against dermatophytes, such as especially representatives of the genera Trichophyton, Epidermophyton and Microsporum, the microorganisms that play a part in dermatophyte infections.
  • FR 2,771 ,632 discloses that specific alkane-1 ,2-diols having a chain length of from 8 to 18 carbon atoms can be used in admixture with an N-acylamino acid as a composition against dandruff or acne.
  • 1 ,2-Octanediol is mentioned as being preferred.
  • this specification does not disclose the action of alkane-1 ,2- diols having a chain length of from C10 to C14 against dermatophytes, such as especially representatives of the genera Trichophyton, Epidermophyton and Microsporum, the microorganisms that play a part in dermatophyte infections.
  • WO 03/000220 (Dragoco Gerberding GmbH & Co. KG) describes the use of 1 ,2- decanediol solely against bacteria that cause body odour. However, this specification contains no reference to an action against dermatophytes, such as especially representatives of the genera Trichophyton, Epidermophyton and Microsporum, the microorganisms that play a part in dermatophyte infections.
  • EP 0 524 548 A1 discloses specific antimicrobially active mixtures which, as well as containing (A) an antimicrobially active aromatic alcohol of formula 1
  • the disclosed antimicrobially active mixtures are described as being suitable for the preparation of antiseptically active skin cleansing agents and for the preservation of aqueous preparations of microbially degradable or perishable substances.
  • this specification contains no reference to an action against dermatophytes, such as especially representatives of the genera Trichophyton, Epidermophyton and Microsporum, the microorganisms that play a part in dermatophyte infections.
  • unbranched 1 ,2-alkanediols having a total chain length of from 5 to 14 carbon atoms and preferably from 6 to 8 carbon atoms are suitable for topical application to the skin and in particular for treating acne, for treating capillary layers, for disinfecting small wounds (scratches), for disinfecting the hands of surgeons and patients and for disinfecting the udders of milk- yielding animals.
  • US 6,123,953 further discloses that formulations which, as well as containing an alkanediol, contain a gel of the glyceryl polymethacrylate type, can be used in a low concentration for treating acne, skin problems, impetigo, microorganism-based body odours, athlete's foot and the like.
  • This usability is attributed to a synergistic interaction between the gel and the alkanediol.
  • 1 ,2-octanediol is named in this specification as the preferred alkanediol for treating acne.
  • This specification does not, however, contain any reference to an action against dermatophytes, such as especially representatives of the genera Trichophyton, Epidermophyton and Microsporum, the microorganisms that play a part in dermatophyte infections.
  • EP 1 598 064 discloses the use of 1 ,2-decanediol in combination with alpha- hydroxy acids in anti-acne products.
  • EP 1 598 064 contains no reference to an action against dermatophytes, such as especially representatives of the genera Trichophyton, Epidermophyton and Microsporum, the microorganisms that play a part in dermatophyte infections.
  • One or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, are preferably used in cosmetic and/or dermatological preparations whose content, in each case based on the total concentration, is from 0.1 to 10 wt.%, more preferably from 0.2 to 5 wt.% and most particularly preferably from 0.5 to 4 wt.%.
  • the dermatophyte In order to penetrate and colonise skin and nails, the dermatophyte must break down the protein structures, some of which are extremely rigid. To this end, the dermatophyte uses peptidases, such as especially specific keratinases, collagenases and elastases, which it releases specifically and which cleave the skin and nail structural proteins into smaller units, permitting penetration and colonisation.
  • Cosmetic preparations containing alkane-1 ,2-diols having a chain length of from C10 to C14 can therefore particularly advantageously also contain active ingredients that are capable of inhibiting the enzymatic activity of peptidases, such as especially matrix metalloproteinases (MMP; elastases and collagenases).
  • MMP matrix metalloproteinases
  • any peptidase inhibitors suitable or conventional for cosmetic and/or dermatological applications can be used. It is advantageous to use one, two, three or more auxiliary substances and/or additives selected from the group consisting of blackberry leaf extract, soya protein and hydrolysed soya protein, soya isoflavones, hydrolysed rice protein, hydrolysed hazelnut protein, wheat protein, b-glucans, preferably from oats and derivatives thereof, glycoproteins, ursolic acid and its salts, betulin, betulinic acid and its salts, retinol, retinol palmitate, epigallocatechin gallate, metastat, batimastat, chlorhexidine, propyl gallate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H)-benzopyran, 3,4- dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1 (2H)-benzopyran, creatine or other synthetic or natural MMP-inhibiting
  • cosmetic preparations containing one or more, preferably one, two or three, C10-C14- alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2- dodecanediol and 1 ,2-tetradecanediol, can particularly advantageously also contain one, two, three or more anti-inflammatory and/or redness- and/or itching- alleviating active ingredients (anti-inflammatories). Any anti-inflammatory and/or redness- and/or itching-alleviating active ingredients suitable or conventional for cosmetic and/or dermatological applications can be used.
  • anti-inflammatory and/or redness- and/or itching-alleviating active ingredients there are advantageously used one, two, three or more steroidal antiinflammatory compounds of the corticosteroid type, preferably hydrocortisone, hydrocortisone derivatives such as hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone, it being possible for this list to be extended by adding further steroidal anti-inflammatories.
  • nonsteroidal anti-inflammatory active ingredients selected from the group consisting of: oxicams, preferably piroxicam or tenoxicam; salicylates, preferably aspirin, disalcid, solprin or fendosal; acetic acid derivatives, preferably diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac; fenamates, preferably mefenamic, meclofenamic, flufenamic or niflumic; propionic acid derivatives, preferably ibuprofen, naproxen, benoxaprofen, or pyrazoles, such as phenylbutazone, oxyphenylbutazone, feprazone or azapropazone.
  • oxicams preferably piroxicam or tenoxicam
  • salicylates preferably aspirin, disalcid, solprin or fendosal
  • acetic acid derivatives preferably di
  • the amount of anti-inflammatory or redness- or itching-alleviating active ingredients (one or more compounds) in the preparations is preferably from 0.0001 to 20 wt.%, particularly preferably from 0.0001 to 10 wt.%, especially from 0.001 to 5 wt.%, in each case based on the total weight of the preparation.
  • One or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, can be used in cosmetic and/or dermatological formulations having very different forms.
  • they can be a solution (e.g.
  • aqueous, aqueous-alcoholic or alcoholic solution an emulsion of the water-in-oil (VWO) or oil-in-water (O/W) type or a multiple emulsion, for example of the water-in-oil-in- water (W/O/W) or oil-in-water-in-oil (0/W/O) type (in each case also in the form of silicone emulsions), a hydrodispersion or lipodispersion, a Pickering emulsion, a solid stick or an aerosol. It can also be advantageous to impregnate a water- insoluble substrate (e.g.
  • C10-C14-alkane-1 ,2- diols according to the invention, it being possible for this form of application to be both a substrate having a dry appearance and a substrate having a moist appearance.
  • Further advantageous forms of administration of the C10-C14- alkane-1 ,2-diols according to the invention are creams, ointments, hydrodispersions, lotions, tinctures, pump sprays, aerosol sprays, aqueous solutions, cleansing substrates, nail lacquers and the like.
  • the aqueous phase can also contain other ingredients, for example alcohols, further diols or polyols having a C number less than 10, and ethers thereof, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products, also alcohols having a low C number, for example ethanol, isopropanol, 1 ,2-propanediol, glycerol, as well as, in particular, one or more thickening agents, which can advantageously be selected from the group silicon dioxide, aluminium silicates, polysaccharides and derivatives thereof, for example hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of the polyacrylates, preferably
  • the C10-C14-alkane-1 ,2-diols according to the invention can be combined with a large number of further auxiliary substances and/or additives, resulting in preferred cosmetic and/or pharmaceutical mixtures or products.
  • Cosmetic and/or dermatological preparations containing one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2-tetradecanediol, can additionally contain one, two or more conventional anti-acne active ingredients, preferably selected from the group consisting of benzoyl peroxide, azelaic acid, salicylic acid, retinoids such as all-trans-retinic acid (tretinoin), all-trans-retinal or cis-13-retinic acid (isotretinoin), as well as antibiotics which are used specifically for the treatment of acne, such as, for example, clindamycin, erythromycin, tetracycline, doxycycline and/or sulfur.
  • antibiotics which are used specifically for the treatment of acne
  • Chlorhexidine, triclosan, bisabolol, farnesol and phenoxyethanol as well as isoflavonoids e.g. genistein, daidzein, genistin and glycitein
  • isoflavonoids e.g. genistein, daidzein, genistin and glycitein
  • One or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, can particularly advantageously additionally be combined with one, two, three or more compounds that regulate skin moisture.
  • Cosmetic preparations containing C10-C14-alkane-1 ,2-diols according to the invention can therefore advantageously additionally contain one, two, three or more humectants selected from the group consisting of: sodium lactate; urea; urea derivatives; alcohols, preferably glycerol, further diols such as propylene glycol, 1 ,2-pentanediol, 1 ,2-hexanediol, hexylene glycol; collagen; elastin or hyaluronic acid; diacyl adipate; petrolatum; urocanic acid; lecithin; panthenol; phytantriol; lycopene; (pseudo)ceramides; glycosphingolipids; cholesterol; phytosterols; chitosan; chondroitin sulfate; lanolin; lanolin esters; amino acids; alpha-hydroxy acids (e.g.
  • citric acid lactic acid, malic acid
  • mono-, di- and oligo-saccharides preferably glucose, galactose, fructose, mannose, fruit sugars and lactose
  • polysugars preferably ⁇ -glucans, in particular 1 ,3-1 ,4- ⁇ - glucan from oats
  • alpha-hydroxy fatty acids preferably triterpenic acid, preferably betulic acid or ursolic acid
  • algae extracts preferably betulic acid or ursolic acid
  • the use concentration of the humectants is in the concentration range from 0.1 to 10 wt.% and preferably in the concentration range from 0.5 to 5 wt.%, in each case based on the total weight of a ready-to- use cosmetic or pharmaceutical end product.
  • Individual cooling active ingredients that are preferably used within the scope of the present invention are listed hereinbelow.
  • cooling active ingredients can also be used in combination with one another: l-menthol, d- menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat®MGA), menthyl lactate (trade name: Frescolat®ML; menthyl lactate is preferably l-menthyl lactate, in particular l-menthyl l-lactate), substituted menthyl- 3-carboxylic acid amides (e.g.
  • menthyl-3-carboxylic acid N-ethylamide 2- isopropyl-N-2,3-trimethylbutanamide, substituted cyclohexanecarboxylic acid amides, 3-menthoxypropane-1 ,2-diol, 2-hydroxyethylmenthyl carbonate, 2- hydroxypropylmenthyl carbonate, N-acetylglycine menthyl ester, isopulegol, menthylhydroxycarboxylic acid esters (e.g.
  • menthyl 3-hydroxy butyrate monomenthyl succinate
  • 2-mercaptocyclodecanone menthyl-2-pyrrolidin-5-one carboxylate
  • 2,3-dihydroxy-p-menthane 3,3,5-trimethylcyclohexanone glycerol ketal
  • 3-menthyl 3,6-di- and -tri-oxaalkanoates 3-menthyl methoxyacetate, icilin.
  • Preferred cooling active ingredients are: l-menthol, d-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat®MGA), menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl l-lactate, trade name: Frescolat®ML), substituted menthyl-3-carboxylic acid amides (e.g.
  • menthyl-3- carboxylic acid N-ethylamide 2-isopropyl-N-2,3-trimethylbutanamide, substituted cyclohexanecarboxylic acid amides, 3-menthoxypropane-1 ,2-diol, 2-hydroxyethylmenthyl carbonate, 2-hydroxypropylmenthyl carbonate, isopulegol.
  • cooling active ingredients are: l-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat®MGA), menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl l-lactate, trade name: Frescolat®ML), 3-menthoxypropane-1 ,2-diol, 2-hydroxyethylmenthyl carbonate, 2-hydroxypropylmenthyl carbonate.
  • cooling active ingredients are: l-menthol, menthone glycerol acetal (trade name: Frescolat®MGA), menthyl lactate (preferably I- menthyl lactate, in particular l-menthyl l-lactate, trade name: Frescolat®ML).
  • the use concentration of the cooling active ingredients that are to be used is preferably in the concentration range from 0.01 to 20 wt. % and more preferably in the concentration range from 0.1 to 5 wt.%, based on the total weight of a ready-to-use cosmetic or pharmaceutical end product.
  • osmolytes examples include: substances from the group of the sugar alcohols (myo-inositol, mannitol, sorbitol), quaternary amines such as taurine, choline, betaine, betaine-glycine, ectoin, diglycerol phosphate, phosphorylcholine, glycerophosphorylcholine, amino acids such as glutamine, glycine, alanine, glutamate, aspartate or proline, phosphatidylcholine, phosphatidylinositol, inorganic phosphates, and also polymers of the mentioned compounds, such as proteins, peptides, polyamino acids and polyols. All osmolytes at the same time have a skin-moisturising action.
  • Caring substances which can be combined with one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2-tetradecanediol, include animal and/or vegetable fats and oils such as olive oil, sunflower oil, refined soya oil, palm oil, sesame oil, rapeseed oil, almond oil, borage oil, evening primrose oil, coconut oil, shea butter, jojoba oil, sperm oil, beef tallow, neat's foot oil and lard, as well as optionally further caring constituents such as, for example, fatty alcohols having from 8 to 30 carbon atoms.
  • the fatty alcohols used can be saturated or unsaturated and linear or branched.
  • Caring substances which can particularly preferably be combined with the C10-C14-alkane-1 ,2-diols according to the invention additionally include in particular also
  • ceramides ceramides being understood as being N-acylsphingosines (fatty acid amides of sphingosine) or synthetic analogues of such lipids (so-called pseudoceramides), which markedly improve the water-retaining capacity of the stratum corneum
  • phospholipids for example soya lecithin, egg lecithin and cephalins
  • vaseline, paraffin and silicone oils include inter alia dialkyl- and alkylaryl-siloxanes such as dimethylpolysiloxane and methylphenylpoly- siloxane, as well as alkoxylated and quaternised derivatives thereof.
  • Cosmetic preparations containing one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2-tetradecanediol, can also contain one, two, three or more active ingredients for preserving cosmetic products as well as perspiration- inhibiting active ingredients (antiperspirants) and (metal) chelators.
  • Preferred (metal) chelators to be used are inter alia ⁇ -hydroxy fatty acids, phytic acid, lactoferrin, ⁇ -hydroxy acids and their salts, preferably citric acid or malic acid, as well as galactaric acid, galacturonic acid, gluconic acid, glucuronic acid, ribonic acid and its salts, humic acids, bile acids, bile extracts, bilirubin, biliverdin or EDTA, EGTA and derivatives thereof.
  • Animal and/or plant protein hydrolysates can advantageously also be added to one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol.
  • animal and/or plant protein hydrolysates are elastin, collagen, keratin, milk protein, soya protein, oat protein, pea protein, almond protein and wheat protein fractions or corresponding protein hydrolysates, as well as the condensation products thereof with fatty acids, and also quaternised protein hydrolysates, the use of plant protein hydrolysates being preferred.
  • a cosmetic and/or dermatological preparation containing one or more, preferably one, two or three, C10-C14-alkanediols according to the invention more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2-tetradecanediol, is a solution or lotion, the following can be used as solvents:
  • esters of fatty acids with alcohols having a low C number e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids having a low C number or with fatty acids;
  • mixtures of the above-mentioned solvents are used.
  • water can be a further constituent.
  • Cosmetic preparations containing one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2-tetradecanediol, can also contain one, two, three or more antioxidants, it being possible to use any antioxidants suitable or conventional for cosmetic and/or dermatological applications.
  • Cosmetic preparations containing one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2-tetradecanediol, can also contain one, two, three or more vitamins and/or vitamin precursors, it being possible to use any vitamins or vitamin precursors suitable or conventional for cosmetic and/or dermatological applications.
  • One or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, can in many cases advantageously be used in combination with one, two, three or more skin-lightening active ingredients. According to the invention, it is possible to use any skin-lightening active ingredients suitable or conventional for cosmetic and/or dermatological applications.
  • Advantageous skin-lightening active ingredients are kojic acid (5-hydroxy-2-hydroxymethyl-4- pyranone), kojic acid derivatives such as, for example, kojic acid dipalmitate, arbutin, ascorbic acid, ascorbic acid derivatives, hydroquinone, hydroquinone derivatives, resorcinol, sulfur-containing molecules such as, for example, glutathione or cysteine, alpha-hydroxy acids (e.g.
  • ⁇ -hydroxy fatty acids palmitic acid, phytinic acid, lactoferrin, humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof), retinoids, soya milk, serine protease inhibitors or liponic acid or other synthetic or natural active ingredients for lightening the skin and hair, it being possible for the latter also to be used in the form of an extract from plants, such as, for example, bearberry extract, rice extract, liquorice root extract or constituents concentrated therefrom, such as glabridine or licochalcone A, Artocarpus extract, extract of Rumex and Ramulus species, extracts from pine species (Pinus) and extracts from Vitis species or concentrated silbene derivatives therefrom, extracts from saxifrage, mulberry, scutelleria and/or grape.
  • an extract from plants such as, for example, bearberry extract, rice extract, liquorice root extract or constituents concentrated
  • Cosmetic preparations containing one or more, preferably one, two or three,
  • C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol,
  • 1 ,2-dodecanediol and 1 ,2-tetradecanediol can also contain one, two, three or more active ingredients having skin-tanning action. It is possible to use any skin- tanning active ingredients suitable or conventional for cosmetic and/or dermatological applications. Examples which may be mentioned here include dihydroxyacetone (DHA; 1 ,3-dihydroxy-2-propanone). DHA can be present in both monomeric and dimeric form, the proportion of dimers being predominant in crystalline form.
  • DHA dihydroxyacetone
  • Cosmetic preparations containing one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2-tetradecanediol, can also contain one, two, three or more mono-, di- and oligo-saccharides, preferably glucose, galactose, fructose, mannose, fruit sugars and lactose.
  • Cosmetic preparations containing one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2-tetradecanediol, can also contain one, two, three or more plant extracts, which are conventionally prepared by extraction of the whole plant but in some cases also solely from blossoms and/or leaves, wood, bark or roots of the plant.
  • Cosmetic preparations containing one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2-tetradecanediol, can, in particular when crystalline or microcrystalline solids, for example inorganic micropigments, are to be incorporated into the preparations, also contain one, two, three or more anionic, cationic, non-ionic and/or amphoteric surfactants.
  • Surfactants are amphiphilic substances which are able to dissolve organic, non-polar substances in water.
  • hydrophilic components of a surfactant molecule are mostly polar functional groups, for example -COO " , -OSO 3 2" , -SO 3 " , while the hydrophobic portions are generally non-polar hydrocarbon radicals.
  • Surfactants are generally classified according to the type and charge of the hydrophilic molecule portion. A distinction can be made between four groups:
  • Anionic surfactants generally contain carboxylate, sulfate or sulfonate groups as functional groups. In aqueous solution they form negatively charged organic ions in an acidic or neutral medium. Cationic surfactants are almost exclusively characterised by the presence of a quaternary ammonium group. In aqueous solution they form positively charged organic ions in an acidic or neutral medium. Amphoteric surfactants contain both anionic and cationic groups and accordingly behave in aqueous solution like anionic or cationic surfactants, depending on the pH value. In a strongly acidic medium they have a positive charge, and in an alkaline medium thay have a negative charge. In the neutral pH range, on the other hand, they are zwitterionic. Typical of non-ionic surfactants are polyether chains. Non-ionic surfactants do not form ions in an aqueous medium.
  • acylamino acids and their salts
  • acyl glutamates for example sodium acyl glutamate, di-TEA palmitoyl aspartate and sodium caprylic/capric glutamate
  • acyl peptides for example palmitoyl-hydrolysed milk protein, sodium cocoyl-hydrolysed soya protein and sodium/potassium cocoyl-hydrolysed collagen
  • sarcosinates for example myristoyl sarcosine, TEA-lauroyl sarcosinate, sodium lauroyl sarcosinate and sodium cocoyl sarcosinate,
  • taurates for example sodium lauroyl taurate and sodium methylcocoyl taurate
  • lauric acid for example lauric acid, aluminium stearate, magnesium alkanolate and zinc undecylenate,
  • ester carboxylic acids for example calcium stearoyl lactylate, laureth-6 citrate and sodium PEG-4 lauramide carboxylate,
  • ether carboxylic acids for example sodium laureth-13 carboxylate and sodium PEG-6 cocamide carboxylate,
  • phosphoric acid esters and their salts such as, for example, DEA-oleth-10 phosphate and dilaureth-4 phosphate,
  • acyl isothionates e.g. sodium/ammonium cocoyl isethionate
  • alkylarylsulfonates for example sodium cocomonoglyceride sulfate, sodium C- 12 - 14 olefin sulfonate, sodium lauryl sulfoacetate and magnesium PEG-3 cocamide sulfate,
  • sulfosuccinates for example dioctyl sodium sulfosuccinate, disodium laureth sulfosuccinate, disodium lauryl sulfosuccinate and disodium undecyleneamido-MEA sulfosuccinate
  • sulfuric acid esters such as
  • alkyl ether sulfate for example sodium, ammonium, magnesium, MIPA, TIPA laureth sulfate, sodium myreth sulfate and sodium C12-13 pareth sulfate,
  • alkyl sulfates for example sodium, ammonium and TEA lauryl sulfate.
  • Quaternary surfactants contain at least one N atom covalently bonded to 4 alkyl or aryl groups. Regardless of the pH value, this results in a positive charge. Alkylbetaine, alkylamidopropylbetaine and alkylamidopropylhydroxysulfain are advantageous.
  • the cationic surfactants used can further preferably be selected from the group of the quaternary ammonium compounds, in particular benzyltrialkylammonium chlorides or bromides, such as, for example, benzyldimethylstearylammonium chloride, also alkyltrialkylammonium salts, for example cetyltrimethylammonium chloride or bromide, alkyldimethylhydroxy- ethylammonium chlorides or bromides, dialkyldimethylammonium chlorides or bromides, alkylamide ethyltrimethylammonium ether sulfates, alkylpyridinium salts, for example lauryl- or cetyl-pyridinium chloride, imidazoline derivatives and compounds of cationic nature such as amine oxides, for example alkyldimethylamine oxides or alkylaminoethyldimethylamine oxides. Cetyltrimethylammonium salts are particularly advantageously to be
  • acyl-/dialkylethylenediamine for example sodium acyl amphoacetate, disodium acyl amphodipropionate, disodium alkyl amphodiacetate, sodium acyl amphohydroxypropylsulfonate, disodium acyl amphodiacetate and sodium acyl amphopropionate, N-alkylamino acids, for example aminopropylalkylglutamide, alkyl- aminopropionic acid, sodium alkylimidodipropionate and lauroamphocar- boxyglycinate.
  • N-alkylamino acids for example aminopropylalkylglutamide, alkyl- aminopropionic acid, sodium alkylimidodipropionate and lauroamphocar- boxyglycinate.
  • alkanolamides such as cocamides MEA/ DEA/ MIPA
  • amine oxides such as cocoamidopropylamine oxide, esters formed by esterification of carboxylic acids with ethylene oxide, glycerol, sorbitan or other alcohols,
  • ethers for example ethoxylated/propoxylated alcohols, ethoxylated/propoxylated esters, ethoxylated/propoxylated glycerol esters, ethoxylated/propoxylated cholesterols, ethoxylated/propoxylated triglyceride esters, ethoxylated propoxylated lanolin, ethoxylated/propoxylated polysiloxanes, propoxylated POE ethers and alkylpolyglycosides such as lauryl glucoside, decyl glycoside and cocoglycoside,
  • sucrose esters sucrose ethers
  • polyglycerol esters diglycerol esters, monoglycerol esters,
  • anionic and/or amphoteric surfactants with one or more non-ionic surfactants.
  • the surface-active substance can be present in the preparations according to the invention containing alkane-1 ,2-diols having a chain length of from C10 to C14 in a concentration of from 1 to 98 wt.%, based on the total weight of the preparations.
  • Emulsions comprising a mixture according to the invention:
  • Cosmetic or dermatological preparations containing alkane-1 ,2-diols having a chain length of from C10 to C14 according to the invention can also be present in the form of emulsions.
  • the oil phase can advantageously be selected from the following group of substances: mineral oils, mineral waxes;
  • esters of fatty acids with alcohols having a low C number e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids having a low C number or with fatty acids;
  • silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • ester oils are 3,5,5-trimethylhexyl-3,5,5-trimethyl hexanoate, 2-ethylhexyl isononanoate, 2-ethylhexyl-3,5,5-trimethyl hexanoate, 2- ethylhexyl-2-ethyl hexanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2- hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate and also synthetic, semi-synthetic and natural mixtures of such esters, for example jojoba oil advantageously be combined with the alkane- 1 ,2-diols having a chain length of from C10 to C14 according to the invention.
  • esters of aromatic carboxylic acids and saturated and/or unsaturated, branched and/or unbranched alcohols having a chain length of from 3 to 30 carbon atoms can also be used.
  • the oil phase can also advantageously be selected from the group of the branched and unbranched hydrocarbons and waxes, the silicone oils, the dialkyl ethers, the group of the saturated or unsaturated, branched or unbranched alcohols, and also of the fatty acid triglycerides, specifically the triglycerol esters of saturated and/or unsaturated, branched and/or unbranched alkanecarboxylic acids having a chain length of from 8 to 24 carbon atoms, in particular from 12 to 18 carbon atoms.
  • the fatty acid triglycerides can advantageously be selected from the group of the synthetic, semi-synthetic and natural oils, e.g.
  • the oil phase is advantageously selected from the group consisting of 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosan, 2-ethylhexyl cocoate, Ci 2- i5-alkyl benzoate, caprylic- capric acid triglyceride and dicaprylyl ether.
  • Ci 2- i5-alkyl benzoate and 2-ethylhexyl isostearate Mixtures of Ci 2- i5-alkyl benzoate and 2-ethylhexyl isostearate, mixtures of Ci 2 -is-alkyl benzoate and isotridecyl isononanoate and mixtures of Ci 2- i5-alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate are particularly advantageous.
  • the hydrocarbons paraffin oil, squalane and squalene can also advantageously be used.
  • the oil phase can advantageously also contain cyclic or linear silicone oils or consist wholly of such oils, it being preferred, however, to use an additional content of other oil-phase components in addition to the silicone oil or silicone oils.
  • Cyclomethicone e.g. decamethylcyclopentasiloxane
  • silicone oil can advantageously be used as the silicone oil.
  • other silicone oils can also advantageously be used, for example undecamethylcyclotrisiloxane, polydimethylsiloxane and poly(methyl-phenylsiloxane).
  • Mixtures of cyclomethicone and isotridecyl isononanoate and also of cyclomethicone and 2-ethylhexyl isostearate are also particularly advantageous.
  • the aqueous phase of preparations in emulsion form that contain alkane-1 ,2- diols having a chain length of from C10 to C14 can advantageously comprise: alcohols, diols or polyols having a low C number, and also ethers thereof, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products, also alcohols having a low C number, e.g.
  • ethanol isopropanol, 1 ,2-propanediol, glycerol, and, in particular, one or more thickening agents, which can advantageously be selected from the group silicon dioxide, aluminium silicates, polysaccharides and derivatives thereof, e.g. hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of the polyacrylates, preferably a polyacrylate from the group of the so-called carbopols, for example carbopols of types 980, 981 , 1382, 2984, 5984, in each case individually or in combination.
  • one or more thickening agents which can advantageously be selected from the group silicon dioxide, aluminium silicates, polysaccharides and derivatives thereof, e.g. hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageously from the group of the polyacrylates, preferably a polyacrylate from the group of the so-called carbopol
  • Preparations in emulsion form that contain alkane-1 ,2-diols having a chain length of from C10 to C14 according to the invention advantageously comprise one or more emulsifiers.
  • O/W emulsifiers can advantageously be selected, for example, from the group of the polyethoxylated or polypropoxylated or polyethoxylated and polypropoxylated products, e.g.:
  • alkyl ether carboxylic acids of the general formula R-COO-(-CH 2 -CH 2 -O-) n -OOH, and n represent a number from 5 to 30,
  • alkyl ether sulfates of the general formula R-O-(-CH 2 -CH 2 -O-) n -SO 3 -H,
  • the polyethoxylated or polypropoxylated or polyethoxylated and polypropoxylated 0/W emulsifiers are particularly advantageously selected from the group of substances having HLB values of from 1 1 to 18, most particularly preferably having HLB values of from 14.5 to 15.5, provided the 0/W emulsifiers contain saturated radicals R and R'. If the 0/W emulsifiers contain unsaturated radicals R and/or R', or if isoalkyl derivatives are present, then the preferred HLB value of such emulsifiers can also be lower or higher.
  • fatty alcohol ethoxylates from the group of the ethoxylated stearyl alcohols, cetyl alcohols, cetyl stearyl alcohols (cetearyl alcohols). Particular preference is given to:
  • Sodium laureth-1 1 carboxylate can advantageously be used as the ethoxylated alkyl ether carboxylic acid or salt thereof.
  • Sodium laureth 1-4 sulfate can advantageously be used as the alkyl ether sulfate.
  • Polyethylene glycol (30) cholesteryl ether can advantageously be used as the cholesterol derivative.
  • Polyethylene glycol (25) soya sterol has also proved suitable.
  • Polyethylene glycol (60) evening primrose glycerides can advantageously be used as ethoxylated triglycerides.
  • polyethylene glycol glycerol fatty acid esters from the group polyethylene glycol (20) glyceryl laurate, polyethylene glycol (21 ) glyceryl laurate, polyethylene glycol (22) glyceryl laurate, polyethylene glycol (23) glyceryl laurate, polyethylene glycol (6) glyceryl caprylate/caprinate, polyethylene glycol (20) glyceryl oleate, polyethylene glycol (20) glyceryl isostearate, polyethylene glycol (18) glyceryl oleate/cocoate.
  • sorbitan esters from the group polyethylene glycol (20) sorbitan monolaurate, polyethylene glycol (20) sorbitan monostearate, polyethylene glycol (20) sorbitan monoisostearate, polyethylene glycol (20) sorbitan monopalmitate, polyethylene glycol (20) sorbitan monooleate.
  • VWO emulsifiers fatty alcohols having from 8 to 30 carbon atoms, monoglycerol esters of saturated and/or unsaturated, branched and/or unbranched alkanecarboxylic acids having a chain length of from 8 to 24 carbon atoms, especially from 12 to 18 carbon atoms, diglycerol esters of saturated and/or unsaturated, branched and/or unbranched alkanecarboxylic acids having a chain length of from 8 to 24 carbon atoms, especially from 12 to 18 carbon atoms, monoglycerol ethers of saturated and/or unsaturated, branched and/or unbranched alcohols having a chain length of from 8 to 24 carbon atoms, especially from 12 to 18 carbon atoms, diglycerol ethers of saturated and/or unsaturated, branched and/or unbranched alcohols having a chain length of from 8 to 24 carbon atoms, especially from 12 to 18 carbon atoms, diglycerol ethers of saturated and/or
  • W/O emulsifiers are glyceryl monostearate, glyceryl monoisostearate, glyceryl monomyristate, glyceryl monooleate, diglyceryl monostearate, diglyceryl monoisostearate, propylene glycol monostearate, propylene glycol monoisostearate, propylene glycol monocaprylate, propylene glycol monolaurate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monocaprylate, sorbitan monoisooleate, saccharose distearate, cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, isobehenyl alcohol, selachyl alcohol, chimyl alcohol, polyethylene glycol (2) stearyl ether (steareth-2), glyceryl monolaurate, glyceryl monocaprinate, glyceryl monocaprylate.
  • cosmetic and/or dermatological preparations which contain one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, and in addition one, two, three or more compounds that act as sun-protection agents.
  • Such preparations advantageously contain at least one UVA filter and/or at least one UVB filter and/or at least one inorganic pigment.
  • the preparations can be present in various forms, such as, for example, are conventionally used for this type of preparation.
  • they can preferably be a solution, an emulsion of the water-in-oil (W/O) or oil-in-water (O/W) type, or a multiple emulsion, for example of the water-in-oil-in-water (W/O/W) type, a gel, a hydrodispersion, a solid stick or alternatively an aerosol.
  • W/O water-in-oil
  • O/W oil-in-water
  • a multiple emulsion for example of the water-in-oil-in-water (W/O/W) type, a gel, a hydrodispersion, a solid stick or alternatively an aerosol.
  • Suitable thickeners are selected from the group consisting of homopolymers of acrylic acid having a molecular weight of from 2,000,000 to 6,000,000, preferably commercial carbopols. Further preferred thickeners are marketed under the names Carbopol 940, Carbopol EDTA 2001 or Modarez V 600 PX.
  • One or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, can advantageously also be combined in cosmetic preparations with one, two, three or more cosmetic auxiliary substances as are conventionally used in such preparations, preferably antioxidants, perfume oils, agents for preventing foaming, colourings, pigments having a colouring action, thickening agents, surface-active substances, emulsifiers, plasticising substances, further moisturising and/or humectant substances, fats, oils, waxes or other conventional constituents of a cosmetic formulation, such as preferably alcohols, polyols, polymers, foam stabilisers, electrolytes, organic solvents or silicone derivatives.
  • antioxidants perfume oils, agents for preventing foaming, colourings, pigments having a colouring action, thickening agents, surface-active substances, emulsifiers, plasticising substances, moisturising and/or humectant substances, fats, oils, waxes, alcohols, polyols, polymers, foam stabilisers, electrolytes, organic solvents or silicone derivatives that are suitable or conventional for cosmetic and/or dermatological applications.
  • the C10-C14-alkane-1 ,2-diols according to the invention can also be used as a constituent of fragrance compositions for hair and scalp care products and in particular, because of their specific activity, can impart, for example, an additional anti-dandruff action to a perfumed finished product.
  • fragrance compositions comprise or consist of (a) a sensorially effective amount of a fragrance or of the sum of two, three or more fragrances, (b) a dermatophyte-inhibiting amount of one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2-tetradecanediol, and (c) optionally one or more carriers and/or additives.
  • a fragrance composition contains approximately from 0.1 to 10 wt.% of one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, in each case based on the total weight.
  • Fragrances which are advantageously suitable for combination are found, for example, in S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, N. J. 1969, author/publisher, or K. Bauer et ai, Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001. The following may be mentioned specifically as being preferred:
  • fragrances from the group of the hydrocarbons such as, for example, 3-carene; ⁇ -pinene; ⁇ -pinene; ⁇ -terpinene; ⁇ -terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E,Z)-1 ,3,5-undecatriene; styrene; diphenylmethane;
  • aliphatic alcohols such as, for example, hexanol; octanol; 3-octanol; 2,6- dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E)-2-hexenol; (E)- and (Z)-3-hexenol; 1-octen-3-ol; mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E,Z)-2,6-nonadienol; 3,7- dimethyl-7-methoxyoctan-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;
  • aliphatic aldehydes and their acetals such as, for example, hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2- methyloctanal; 2-methylnonanal; (E)-2-hexenal; (Z)-4-heptenal; 2,6-dimethyl-5- heptenal; 10-undecenal; (E)-4-decenal; 2-dodecenal; 2,6,10-trimethyl-9- undecenal; 2,6,10-trimethyl-5,9-undecadienal; heptanaldiethylacetal; 1 ,1- dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; 1 -(1 -methoxy- propoxy)-(E/Z)-3-hexene; of the aliphatic ketones and their acetal
  • aliphatic sulfur-containing compounds such as, for example, 3-methylthio- hexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol;
  • aliphatic nitriles such as, for example, 2-nonenoic acid nitrile; 2- undecenoic acid nitrile; 2-tridecenoic acid nitrile; 3,12-tridecadienoic acid nitrile; 3,7-dimethyl-2,6-octadienoic acid nitrile; 3,7-dimethyl-6-octenoic acid nitrile;
  • esters of aliphatic carboxylic acids such as, for example, (E)- and (Z)-3- hexenyl formate; ethyl acetoacetate; isoamyl acetate; hexyl acetate; 3,5,5- trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E)-2-hexenyl acetate; (E)- and (Z)-3-hexenyl acetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl butyrate; hexyl butyrate; (E)- and (Z)-3- hexenyl isobutyrate; hexyl crotonate; ethyl isovalerate; ethyl-2-methyl pentanoate; ethyl isova
  • acyclic terpene alcohols such as, for example, citronellol; geraniol; nerol; linalool; lavandulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6- dimethyl-7-octen-2-ol; 2,6-dimethyloctan-2-ol; 2-methyl-6-methylene-7-octen-2- ol; 2,6-dimethyl-5,7-octadien-2-ol; 2,6-dimethyl-3,5-octadien-2-ol; 3,7-dimethyl- 4,6-octadien-3-ol; 3,7-dimethyl-1 ,5,7-octatrien-3-ol; 2,6-dimethyl-2,5,7-octatrien- 1-ol; and their formates, acetates, propionates, isobutyrates,
  • cyclic terpene alcohols such as, for example, menthol; isopulegol; alpha- terpineol; terpinenol-4; menthan-8-ol; menthan-1-ol; menthan-7-ol; borneol; isoborneol; linalool oxide; nopol; cedrol; ambrinol; vetiverol; guaiol; and their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates, 3-methyl-2-butenoat.es;
  • cyclic terpene aldehydes and ketones such as, for example, menthone; isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchone; alpha- ionone; beta-ionone; alpha-n-methylionone; beta-n-methylionone; alpha- isomethylionone; beta-isomethylionone; alpha-irone; alpha-damascone; beta- damascone; beta-damascenone; delta-damascone; gamma-damascone; 1- (2,4,4-trimethyl-2-cyclohexen-1 -yl)-2-buten-1 -one; 1 ,3,4,6,7,8a-hexahydro-
  • cyclic alcohols such as, for example, 4-tert.-butylcyclohexanol; 3,3,5- trimethylcyclohexanol; 3-isocamphylcyclohexanol; 2,6,9-trimethyl-Z2,Z5,E9- cyclododecatrien-1 -ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;
  • cycloaliphatic alcohols such as, for example, alpha-3,3- trimethylcyclohexylmethanol; 1 -(4-isopropylcyclohexyl)ethanol; 2-methyl-4-(2,2,3- trimethyl-3-cyclopent-1 -yl)butanol; 2-methyl-4-(2,2,3-trimethyl-3-cyclopent-1 -yl)- 2-buten-1-ol; 2-ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl)-pentan-2-ol; 3-methyl-5-(2,2,3-trimethyl-3- cyclopent-1 -yl)-4-penten-2-ol; 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1 -yl)-4- penten-2-ol; 1 -(2,2,6-trimethylcyclohexy
  • cyclic and cycloaliphatic ethers such as, for example, cineol; cedryl methyl ether; cyclododecyl methyl ether; 1 ,1-dimethoxycyclododecane;
  • cyclic and macrocyclic ketones such as, for example, 4-tert- butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclo- pentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3- methyl-cis-2-penten-1 -yl-2-cyclopenten-1 -one; 3-methyl-2-pent.yl-2-cyclopent.en- 1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3- methylcyclopentadecanone; 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone; 4-tert.-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1 ,1 ,2,3,3- pentamethyl-4(5H)-in
  • cycloaliphatic aldehydes such as, for example, 2,4-dimethyl-3- cyclohexenecarbaldehyde; 2-methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2- butenal; 4-(4-hydroxy-4-methylpentyl)-3-cyclohexenecarbaldehyde; 4-(4-methyl- 3-penten-1 -y ⁇ -S-cyclohexenecarbaldehyde;
  • cycloaliphatic ketones such as, for example, 1-(3,3-dimethylcyclohexyl)-4- penten-1 -one; 2,2-dimethyl-1 -(2,4-dimethyl-3-cyclohexen-1 -yl)-1 -propanone; 1 - (5,5-dimethyl-1 -cyclohexen-1 -yl)-4-penten-1 -one; 2,3,8,8-tetramethyl- 1 ,2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; methyl 2,6,10-trimethyl- 2,5,9-cyclododecatrienyl ketone; tert.
  • esters of cycloaliphatic alcohols such as, for example, 1-cyclohexylethyl crotonate
  • esters of cycloaliphatic carboxylic acids such as, for example, allyl-3- cyclohexyl propionate; allylcyclohexyloxy acetate; cis- and trans-methyl dihydrojasmonate; cis- and trans-methyl jasmonate; methyl 2-hexyl-3- oxocyclopentanecarboxylate; ethyl 2-ethyl-6,6-dimethyl-2-cyclohexene- carboxylate; ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; ethyl 2-methyl- 1 ,3-dioxolan-2-acetate;
  • araliphatic alcohols such as, for example, benzyl alcohol; 1-phenylethyl alcohol; 2-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2- phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3-(3-methyl- phenyl)propanol; 1 ,1-dimethyl-2-phenylethyl alcohol; 1 ,1-dimethyl-3-phenyl- propanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3- methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1-(4- isopropylphenyl)ethanol;
  • esters of araliphatic alcohols and aliphatic carboxylic acids such as, for example, benzyl acetate; benzyl propionate; benzyl isobutyrate; benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; alpha- trichloromethylbenzyl acetate; alpha, alpha-dimethylphenylethyl acetate; alpha,alpha-dimethylphenylethyl butyrate; cinnamyl acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
  • araliphatic ethers such as, for example, 2-phenylethyl methyl ether; 2- phenylethyl isoamyl ether; 2-phenylethyl 1-ethoxyethyl ether; phenylacetaldehyde dimethyl acetal; phenylacetaldehyde diethyl acetal; hydratropaaldehyde dimethyl acetal; phenylacetaldehyde glycerol acetal; 2,4,6- trimethyl-4-phenyl-1 ,3-dioxane; 4,4a,5,9b-tetrahydroindeno[1 ,2-d]-m-dioxine; 4,4a,5,9b-tetrahydro-2,4-dimethylindeno[1 ,2-d]-m-dioxine;
  • aromatic and araliphatic aldehydes such as, for example, benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; hydratropaaldehyde; 4-methyl- benzaldehyde; 4-methylphenylacetaldehyde; 3-(4-ethylphenyl)-2,2-dimethyl- propanal; 2-methyl-3-(4-isopropylphenyl)propanal; 2-methyl-3-(4-tert.-butyl- phenyl)propanal; 2-methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert.-butylphenyl)- propanal; cinnamaldehyde; alpha-butylcinnamaldehyde; alpha-amylcinnam- aldehyde; alpha-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal;
  • aromatic and araliphatic ketones such as, for example, acetophenone; 4- methylacetophenone; 4-methoxyacetophenone; 4-tert.-butyl-2,6-dimethyl- acetophenone; 4-phenyl-2-butanone; 4-(4-hydroxyphenyl)-2-butanone; 1-(2- naphthalenyl)ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl)- ethanone; benzophenone; 1 ,1 ,2,3,3,6-hexamethyl-5-indanyl methyl ketone; 6- tert.-butyl-1 , 1 -dimethyl-4-indanyl methyl ketone; 1-[2,3-dihydro-1 ,1 ,2,6- tetramethyl-3-(1 -methylethyl)-1 H-5-indenyl]ethanone; 5',6',7',8'-tetrahydr
  • aromatic and araliphatic carboxylic acids and their esters such as, for example, benzoic acid; phenylacetic acid; methyl benzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methylphenyl acetate; ethylphenyl acetate; geranylphenyl acetate; phenylethyl-phenyl acetate; methyl cinnamate; ethyl cinnamate; benzyl cinnamate; phenylethyl cinnamate; cinnamyl cinnamate; allylphenoxy acetate; methyl salicylate; isoamyl salicylate; hexyl salicylate; cyclohexyl salicylate; cis-3-hexenyl salicylate; benzyl salicylate; phenylethyl salicylate; methyl-2,4-dihydroxy
  • nitrogen-containing aromatic compounds such as, for example, 2,4,6- trinitro-1 ,3-dimethyl-5-tert.-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert.- butylacetophenone; cinnamic acid nitrile; 3-methyl-5-phenyl-2-pentenoic acid nitrile; 3-methyl-5-phenylpentanoic acid nitrile; methyl anthranilate; methyl-N- methyl anthranilate; Schiff's bases of methyl anthranilate with 7-hydroxy-3,7- dimethyloctanal, 2-methyl-3-(4-tert.-butylphenyl)propanal or 2,4-dimethyl-3- cyclohexenecarbaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec- butylquinoline; 2-(3-phenylpropyl)pyridine; indole;
  • phenols, phenyl ethers and phenyl esters such as, for example, estragole; anethole; eugenol; eugenyl methyl ether; isoeugenol; isoeugenyl methyl ether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-naphthyl ethyl ether; beta-naphthyl isobutyl ether; 1 ,4-dimethoxybenzene; eugenyl acetate; 2- methoxy-4-methylphenol; 2-ethoxy-5-(1-propenyl)phenol; p-cresylphenyl acetate;
  • heterocyclic compounds such as, for example, 2,5-dimethyl-4-hydroxy-2H- furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H- pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;
  • lactones such as, for example, 1 ,4-octanolide; 3-methyl-1 ,4-octanolide; 1 ,4-nonanolide; 1 ,4-decanolide; 8-decen-1 ,4-olide; 1 ,4-undecanolide; 1 ,4- dodecanolide; 1 ,5-decanolide; 1 ,5-dodecanolide; 4-methyl-1 ,4-decanolide; 1 ,15- pentadecanolide; cis- and trans-1 1-pentadecen-1 ,15-olide; cis- and trans-12- pentadecen-1 ,15-olide; 1 ,16-hexadecanolide; 9-hexadecen-1 ,16-olide; 10-oxa- 1 ,16-hexadecanolide; 1 1-oxa-1 ,16-hexadecanolide; 12-oxa-1 ,
  • Preferred carriers are ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1 ,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate and triacetin.
  • One or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, can be incorporated without difficulty into conventional cosmetic or dermatological/keratological formulations such as, inter alia, sprays (pump sprays, aerosol sprays, e.g. foot sprays), creams (e.g. hand creams, foot creams), shampoos, ointments, tinctures, lotions, balsams (e.g.
  • Cosmetic and/or dermatological/keratological formulations containing one or more, preferably one, two or three, C10-C14-alkanediols according to the invention, more preferably a compound or a mixture of two or three compounds from the group consisting of 1 ,2-decanediol, 1 ,2-dodecanediol and 1 ,2- tetradecanediol, can otherwise be composed in the conventional manner and can be used to treat the skin and/or hair within the scope of a dermatological/keratological treatment or a treatment within the scope of caring cosmetics.
  • Trichophyton mentagrophytes strain CBS26379 was used as the test organism.
  • agar plates were cast per test concentration and nutrient medium.
  • test plates were inoculated punctually with in each case 1 ⁇ l of the Trichophyton mentagrophytes
  • 1 ,2-dodecanediol was found to have the greatest activity against Trichophyton mentagrophytes; 1 ,2- decanediol and 1 ,2-tetradecanediol are also to be classified in the category of agents for the treatment of dermatophyte infections that have very good activity against Trichophyton mentagrophytes.
  • the antimicrobial action of the alkane-1 ,2-diols against Epidermophyton floccosum was determined by means of the agar dilution method in accordance with DIN 58 940/ICS and DIN 58 944/ICS.
  • Epidermophyton floccosum strain CBS 55384 was used as the test organism.
  • Petri dishes having a diameter of 9 cm and containing 8.7 ml of freshly prepared Mueller-Hinton agar (Merck, art. 1.05437) kept liquid at 5O 0 C were used.
  • ethanolic stock solutions of the alkane-1 ,2-diol samples were diluted with 96 % ethanol until the following final test concentrations of the alkane-1 ,2-diols in the Mueller-Hinton agar were present: 25,000 ppm, 12,500 ppm, 6300 ppm, 3600 ppm, 1800 ppm, 1100 ppm, 900 ppm, 450 ppm, 225 ppm, 112 ppm, 56 ppm, 28 ppm, 14 ppm, 7 ppm, 4 ppm. 2 agar plates were cast per test concentration and nutrient medium.
  • test plates were inoculated punctually with in each case 1 ⁇ l of the Epidermophyton floccosum
  • the activity of 1 ,2-decanediol which has an MIC value of 112 ppm, is greater than that of 1 ,2-octanediol (MIC value: 900 ppm) by a factor of about 8.
  • 1 ,2-dodecanediol was found to have the greatest activity against Epidermophyton floccosum; 1 ,2-decanediol and 1 ,2-tetradecanediol are also to be classified in the category of agents for the treatment of dermatophyte infections that have very good activity against Epidermophyton floccosum.
  • compositions for the treatment of dermatophyte infections combinations containing a compound or a mixture of two or three compounds selected from the group consisting of 1 ,2-decanediol, 1 ,2- dodecanediol and 1 ,2-tetradecanediol:

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Abstract

La présente invention concerne l'utilisation de C10-C14-alcane-1,2-diols non ramifiés pour l'élaboration d'une composition destinée à la prophylaxie et/ou le traitement d'infections à dermatophytes, et des préparations cosmétiques et/ou dermatologiques pour application locale à base de C10-C14-alcane-1,2-diols.
PCT/EP2007/060918 2006-10-20 2007-10-12 Utilisation de c10-c14-alcane-1,2-diols pour l'élaboration d'une composition destinée à la prophylaxie et/ou le traitement d'infections à dermatophytes Ceased WO2008046796A2 (fr)

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US20120100080A1 (en) * 2010-10-26 2012-04-26 Quinnova Pharmaceuticals, Inc. Econazole Composition and Methods of Treatment Therewith
EP2730271A1 (fr) * 2012-11-11 2014-05-14 Symrise AG Compositions aqueuses
JP2015504853A (ja) * 2011-12-06 2015-02-16 ユニリーバー・ナームローゼ・ベンノートシヤープ 抗菌性組成物
EP3292758A1 (fr) * 2016-09-07 2018-03-14 Rottapharm S.p.A. Composition antimicrobienne comprenant un acide carboxylique et deux diols
US20180344598A1 (en) * 2017-06-05 2018-12-06 The Procter & Gamble Company Hair care compositions comprising materials that modify sebum
WO2020151812A1 (fr) * 2019-01-23 2020-07-30 Symrise Ag Procédé de préparation de 1,2 alcanediols sous une forme galénique solide
CN112494422A (zh) * 2020-12-02 2021-03-16 湖北沃德利派生物科技有限公司 一种缓释微乳温敏抗菌凝胶
CN115919919A (zh) * 2022-12-08 2023-04-07 四川省畜牧科学研究院 抑制皮肤癣菌的组合物及其用途
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US20120101140A1 (en) * 2010-10-26 2012-04-26 Quinnova Pharmaceuticals, Inc. Econazole Composition and Methods of Treatment Therewith
US9358209B2 (en) 2010-10-26 2016-06-07 Exeltis Usa Dermatology, Inc. Econazole composition and methods of treatment therewith
US10543172B2 (en) * 2010-10-26 2020-01-28 Paragon Nordic Ab Econazole composition and methods of treatment therewith
US20120100080A1 (en) * 2010-10-26 2012-04-26 Quinnova Pharmaceuticals, Inc. Econazole Composition and Methods of Treatment Therewith
JP2015504853A (ja) * 2011-12-06 2015-02-16 ユニリーバー・ナームローゼ・ベンノートシヤープ 抗菌性組成物
EP2730271A1 (fr) * 2012-11-11 2014-05-14 Symrise AG Compositions aqueuses
US9468644B2 (en) 2012-11-11 2016-10-18 Symrise Ag Aqueous compositions
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US11998517B2 (en) 2016-09-07 2024-06-04 Rottapharm Spa Antimicrobial composition
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EP3292758A1 (fr) * 2016-09-07 2018-03-14 Rottapharm S.p.A. Composition antimicrobienne comprenant un acide carboxylique et deux diols
US10912747B2 (en) 2016-09-07 2021-02-09 Rottapharm Spa Antimicrobial composition
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US20180344598A1 (en) * 2017-06-05 2018-12-06 The Procter & Gamble Company Hair care compositions comprising materials that modify sebum
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